Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
26.1.4.5.1 Variation 1: With Organosilicon or Organoboron Reagents

DOI: 10.1055/sos-SD-026-00142

Figadère, B.; Franck, X.Science of Synthesis, (200526272.

Thioesters bearing S-alkyl, and S-aryl groups react with boronic acids to give excellent yields of the corresponding ketones. Unlike the case with SuzukiMiyaura couplings, the presence of a base is detrimental, so these reactions are conducted under base-free conditions. The coupling reactions proceed in the presence of a catalytic amount of tris(di­benzylideneacetone)dipalladium(0), tri-2-furylphosphine, and copper(I) thiophene-2-carboxylate (1.6 equiv) in tetrahydrofuran at 50°C to give ketones 48 (Scheme 45).[‌199‌]

Meeeee 88 Meeeeeee ee Meeeeeeeeee Meeeeeee ee Meeeeeeeee[‌888‌]

Meeeeee eeeeeeeeeee eeeeeeee, eeeeeeeeeeeee eeeeeeeeeee eee eeee ee eeee ee eee eeeeeeeee ee eeeeeee. Meee, eeeeeeeee ee ee M-eeeee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeeeeeeeeeee eeeee e eeee eeeee ee eee eeeeeeeeeeeee eeeee­eee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 88 ee Meeeeeee ee Meeeeeeeeee Meeeeeee ee Meeeeeeeee: Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeee (8.8eeee), eeeeee(M) eeeeeeeee-8-eeeeeeeeeee (8.888e, 8.88eeee), eee eeeeeeeeeee eeee (8.88eeee), Me8(eee)8MMMe8 (8.888e, 8.888eeee), eee eee-8-eeeeeeeeeeeeee (8.888e, 8.888eeee) eeee eeeeee ee eeeeeeee eeeeee eeee eee eeeeeee eeee eeeee. MMM (8eM) eee eeeee eee eee eeeeeee eee eeeeeee ee 88°M eee 88e. Me8M (88eM) eee eeeee eee eee eeeeeeeeee eee eeeeee eeee 8% ee MMe (88eM) eee M8M (88eM). Mee eeeeeee eeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeee. Mee eeeeeeeee eeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee [Meeeeeeeeeee, eeeeee eee eeeee (8ee), eeeeeee/Me8M eeeeeeee].

References